Sulfuric Acid → HCID 58525572, compound

Participants

Reaction Conditions

Reaction Steps

6-Hydroxyquinoline-3-carboxylic acid (Int-15, 1 g, 5.29 mmol) was suspended in methanol (25 mL) to which sulfuric acid (0.3 mL, 5 mmol) was carefully added. The reaction was heated at 70° C. under an atmosphere of nitrogen for 48 h. The reaction was cooled to room temperature and saturated sodium bicarbonate solution (2 mL) was added. The solvent was removed under reduced pressure and the crude residue was co-evaporated with toluene twice. The dried residue was purified by silica gel chromatography (methylene chloride to 95/5 methylene chloride/methanol gradient) to afford Int-16 (0.89 g, 83%). LC-MS: (FA) ES+ 204; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.23 (d, J=1.7 Hz, 1H), 9.09 (s, 1H), 8.05 (d, J=9.1 Hz, 1H), 7.59 (dd, J=9.1, 2.5 Hz, 1H), 7.50 (d, J=2.5 Hz, 1H), 3.96 (s, 3H).

Provenance & Evidence